CN107849410A - Pressure-sensitive adhesion Polarizer - Google Patents

Pressure-sensitive adhesion Polarizer Download PDF

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Publication number
CN107849410A
CN107849410A CN201680040235.0A CN201680040235A CN107849410A CN 107849410 A CN107849410 A CN 107849410A CN 201680040235 A CN201680040235 A CN 201680040235A CN 107849410 A CN107849410 A CN 107849410A
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China
Prior art keywords
pressure
formula
compound
bigger
sensitive adhesive
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CN201680040235.0A
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CN107849410B (en
Inventor
朴亨淑
梁世雨
孙贤喜
尹苏罗
韩素吉
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Shanjin Photoelectric Guangzhou Co ltd
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LG Chemical Co Ltd
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    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133528—Polarisers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/485—Polyethers containing oxyethylene units and other oxyalkylene units containing mixed oxyethylene-oxypropylene or oxyethylene-higher oxyalkylene end groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2170/00—Compositions for adhesives
    • C08G2170/40—Compositions for pressure-sensitive adhesives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer

Abstract

Can provide in this application for example allow pressure sensitive adhesive layer and another layer in Polarizer have excellent interfacial adhesion and without segregation phenomenon pressure-sensitive adhesion Polarizer as pressure-sensitive adhesion Polarizer.

Description

Pressure-sensitive adhesion Polarizer
Technical field
This application claims on July 10th, 2015 korean patent application submitted the 10-2015-0098206th and in On April 10th, 2016 korean patent application submitted the 10-2016-0040353rd priority and rights and interests, the disclosure of which leads to Reference is crossed to be integrally incorporated herein.
The application is related to pressure-sensitive adhesion Polarizer.
Background technology
Cross-linkable composition is just used in multiple fields.For example, contact adhesive or adhesive can be applied that will protect Film or optical element be attached to such as on the element of liquid crystal display (LCD) panel with prevent optical element such as Polarizer, its There is cut in the adhering contaminant such as his plastic product, household electrical appliance, automobile such as dust, and here, this pressure-sensitive adhesion Agent or adhesive can be formed by cross-linkable composition.
With what is formed in advance in one surface by using the pressure-sensitive adhesive composition in cross-linkable composition The optical element of pressure sensitive adhesive layer is referred to as pressure-sensitive adhesion optical element.For example, as disclosed in patent document 1, it is this Pressure-sensitive adhesion optical element, which generally has, is included in what support substrate was formed on a surface such as Polarizer, polarization element The structure of pressure sensitive adhesive layer.
In pressure-sensitive adhesion optical element as described above, it is necessary to ensure that support substrate such as Polarizer and contact adhesive Cohesive between layer, and should also suppress the generation of contact adhesive separation.
Prior art literature
Patent document
(patent document 1) Japanese Patent No. 5019552
The content of the invention
Technical purpose
The application is related to pressure-sensitive adhesion Polarizer, and for example, be related to allow pressure sensitive adhesive layer in Polarizer with it is another One layer has excellent interfacial adhesion and without the pressure-sensitive adhesion Polarizer of segregation phenomenon.
Technical scheme
The application is related to pressure-sensitive adhesion optical element.In pressure-sensitive adhesion optical element, when optical element is Polarizer, Optical element is referred to alternatively as pressure-sensitive adhesion Polarizer.
Therefore, pressure-sensitive adhesion optical element may include optical element and be formed on a surface of the optical element Pressure sensitive adhesive layer.When optical element is pressure-sensitive adhesion Polarizer, optical element can be polarization element.Pressure sensitive adhesive layer can Include the polyalkylene polyol compound for being 10000 or bigger with 3 or more hydroxyls and weight average molecular weight.
Such pressure sensitive adhesive layer can be formed by cross-linkable composition explained below.For example, pressure sensitive adhesive layer Can be by making organic solvent be volatilized from above-mentioned cross-linkable composition and forming acrylic psa resin crosslinks. In addition, in the above description, pressure-sensitive adhesion optical element can instigate optical element is attached to by pressure sensitive adhesive layer and glued Thing and the optical element formed.
In the above description, for example, the example of optical element includes light polarizing film, brightness enhancement film, phase shift films etc. without special Limitation, and can typically use light polarizing film.
In the above description, the type of light polarizing film is not particularly limited, and for example, can be used known in the art common The light polarizing film of type is such as the light polarizing film based on polyvinyl alcohol without limiting.
Light polarizing film is that the light vibrated in one direction can be only extracted from the incident light vibrated in a plurality of directions Functional membrane.In such light polarizing film, for example, dichroic dye can be adsorbed and arranged by the resin film based on polyvinyl alcohol.Shape The resin based on polyvinyl alcohol into light polarizing film can be resin gelled and acquisition based on polyvinyl acetate for example by making. In this case, the resin to be used based on polyvinyl acetate can also include vinyl acetate and can be with the acetic acid second The copolymer of monomer and the homopolymer of vinyl acetate of alkene ester copolymerization.With the monomer of vinyl acetate copolymerization can be able to be but The one kind or extremely being not limited in unsaturated carbon acid ester, alkene, vinyl ethers, unsaturated sulfonic acid ester and acrylamide with ammonium Few two kinds mixture.It can be about 85mol% to 100mol% generally, based on the jelly grade of the resin of polyvinyl alcohol, and It is preferred that 98mol% or bigger.Resin based on polyvinyl alcohol can be further modified, and for example, can be to gather through what aldehyde was modified Vinyl formal or polyvinyl acetal.In addition, the extent of polymerization of the resin based on polyvinyl alcohol can be about 1000 to 10000 or 1500 to 5000.
Light polarizing film can be prepared by the following procedure：The resin film based on polyvinyl alcohol is set to be orientated (for example, uniaxial orientation), with two colors Property dyestuff by based on polyvinyl alcohol resin film dye, adsorb dichroic dye, with boric acid aqueous solution handle be adsorbed with dichroism The resin film based on polyvinyl alcohol of dyestuff, is washed out polyvinyl alcohol resin film.Here, as dichroic dye, can be used Iodine or dichroism organic pigment.
When optical element is light polarizing film, optical element, which may also include, to be attached on one or two surface of light polarizing film Diaphragm, and in this case, pressure sensitive adhesive layer can be formed on a surface of diaphragm.The type of diaphragm does not have There is special limitation, and the example includes the film based on cellulose, such as triacetyl cellulose (TAC) film；Film based on polyester, Such as makrolon or poly- (ethylene glycol terephthalate) (PET) film；Acrylic film；Film based on polyether sulfone；And have Containing polyethylene film, polypropylene screen and film based on polyolefin (using having resin or second based on ring or ENB structure It is prepared by alkene-propylene copolymer) one of or at least film of both stacked structures.
In this application, the method that pressure sensitive adhesive layer is formed on above-mentioned optical element is not particularly limited, and example Such as, the method for preparing contact adhesive can be applied, and can also be used and pressure-sensitive adhesive composition is applied directly to Polarizer The method for going up and making it to solidify, or pressure-sensitive adhesive composition is coated on the release-treated surface of peelable film simultaneously The method for solidifying it and resulting composition being transferred to Polarizer.
Layer of the surface through processing can be comprised additionally in by being attached with the surface of the optical element of pressure sensitive adhesive layer, such as through corona The layer of processing or plasma-treated layer.Layer of the surface through processing has hydroxyl, its can by with isocyanates chemical combination Thing etc. reacts and improves interfacial adhesion.
In this application, above-mentioned polyalkylene polyol chemical combination can be included by forming the cross-linkable composition of pressure sensitive adhesive layer Thing.Cross-linkable composition can also include acrylic psa resin and for the acrylic psa resin Crosslinking agent as linked.In this application, a certain component included in cross-linkable composition can be interpreted to include A certain component in pressure sensitive adhesive layer.However, when component is included in pressure sensitive adhesive layer, component can be at and component The different state of state during included in cross-linkable composition.For example, acrylic psa resin and crosslinking agent exist Uncrosslinked state is in cross-linkable composition, and they are in cross-linked state in pressure sensitive adhesive layer.Cross-linkable composition Can be by being used as the acrylic psa resin of main cross-linking reaction and between the crosslinking agent of pressure sensitive adhesive resin Cross-linking reaction and be crosslinked.The present inventor confirms, when the cross-linking reaction during film is formed by cross-linkable composition When carrying out too fast, it is impossible to suitably ensure the interfacial adhesion between the film that is consequently formed and another film.Therefore, in the application In, it is found that the polyalkylene polyol compound in cross-linkable composition is included in suitably to suppress crosslinking instead by designing Should, the speed of cross-linking reaction is properly controlled, and thus cross-linkable composition can be formed has good interface with another film The film of cohesive and without segregation phenomenon etc..
In this manual, term " polyalkylene polyol compound " refers to polyalkylene oxide units and 3 or more The compound of multiple hydroxyls.In the above description, hydroxyl may be present in the end of polyalkylene polyol compound.
In this manual, unless otherwise specified, otherwise when measurement temperature can influence its income value, corresponding institute The value that must be worth to measure at room temperature.Term " room temperature " used herein is the natural temperature not being raised and lowered, and can About in the range of 10 DEG C to 30 DEG C, or it is about 23 DEG C or about 25 DEG C.
Acrylic psa resin included in cross-linkable composition is as master comprising acrylic monomer Want component and the polymer of sensitive adhesive properties can be shown before or after crosslinking.In the above description, acrylic compounds Monomer can be acrylic or methacrylic acid, acrylic or methacrylic acid derivative, and for example, can be acrylate or Methacrylate.It is 55% or more comprising the weight ratio for representing respective components as key component in addition, in this application Greatly, 60% or bigger, 65% or bigger, 70% or bigger, 75% or bigger, 80% or bigger, 85% or bigger or 90% It is or bigger.In another embodiment, as key component by comprising component weight ratio can be 100% or smaller, or Less than 100%.
Acrylic psa resin can be used as key component to be included in cross-linkable composition.Namely based on can hand over Join the total solid content of composition, the weight ratio of acrylic psa resin can be 55% or bigger, 60% or bigger, 65% or bigger, 70% or bigger, 75% or bigger, 80% or bigger, 85% or bigger or 90% or bigger.In another reality Apply in scheme, the total solid content based on cross-linkable composition, the weight ratio of resin is alternatively 100% or smaller or less than 100%.
As acrylic psa resin, for example, the acrylic psa tree with carboxyl can be used Fat.The present inventor confirms that the pressure sensitive adhesive resin with carboxyl as crosslinkable component is for meeting below to The energy relationship of description is favourable.
In addition, this acrylic psa resin can improve cross-linkable composition under the conditions of heat-resisting and wet-heat resisting Durability, and in the case where adding ionic compound explained below, sheet resistance can be formed due to the compound And change over time the film of very little.In addition, it is specifically for use in the LCD of so-called vertical orientated (VA) pattern pressure-sensitive adhesion optics Element can obtain good effect by using the acrylic psa resin.
In one embodiment, the acid number of acrylic psa resin can be 20 or bigger.In above description In, acid number represents to neutralize the milligram number of the potassium hydroxide needed for the free fatty or resin acid included in 1g samples.Another In individual embodiment, the acid number of resin can be about 25 or bigger or about 30 or bigger.In addition, in another embodiment, The acid number of resin can be about 50 or smaller, about 45 or smaller, about 40 or smaller or about 35 or smaller.Have by application above-mentioned The resin of acid number, the carboxylic effect of bag can be further enhanced.
As acrylic psa resin, for example, the polymerization list with (methyl) acrylate monomer can be used The polymer of the polymerized unit of member and acid monomer.In this manual, term " polymerized unit " can refer to wherein corresponding monomer The state of polymer backbone is formed by polymerisation.
In the above description, as (methyl) acrylate compounds, for example, (methyl) alkyl acrylate can be used, And it is contemplated that control cohesive force, glass transition temperature, sensitive adhesive properties etc. and contains 2 to 12 carbon originals using having (methyl) alkyl acrylate of the alkyl of subnumber.The example of this monomer includes (methyl) methyl acrylate, (methyl) propylene Acetoacetic ester, (methyl) n-propyl, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) acrylic acid The tert-butyl ester, methyl) sec-butyl acrylate, (methyl) amyl acrylate, (methyl) 2-EHA, (methyl) acrylic acid 2- ethyls butyl ester, (methyl) n-octyl, (methyl) isobornyl acrylate, (methyl) Isooctyl acrylate monomer, (methyl) The different nonyl ester of acrylic acid, (methyl) lauryl acrylate etc., and it is a kind of or two or more can be included in polymer.
For example, acrylic psa resin can include acid monomer as polymerized unit.Term " acid monomer " Refer to the polymerisable monomer with acidic-group, and for example, the monomer with carboxyl can be used.In the above description, have The example of the monomer of carboxyl includes (methyl) acrylic acid, 2- (methyl) acryloxyacetic acid, 3- (methyl) acryloxy third Acid, 4- (methyl) acryloxies butyric acid, acrylic acid dimer, itaconic acid, maleic acid, maleic anhydride etc., but not limited to this.
(methyl) acrylate compounds based on 100 parts by weight, acrylic psa resin can include about 5 weights The acid monomer of part or more, 5.5 parts by weight or more or 6 parts by weight or more is measured as polymerized unit.In this specification In, unless otherwise specified, otherwise term " parts by weight " can refer to the weight ratio between component.In another embodiment, It can be included with about 20 parts by weight or smaller, about 15 parts by weight or smaller or about 10 parts by weight or smaller ratio acid single Body.
If necessary, acrylic psa resin can include the other polymerized unit of monomer, and the monomer is for example Monomer comprising hydroxyl, for example, (methyl) hydroxyalkyl acrylates, such as (methyl) acrylic acid 2- hydroxy methacrylates, (methyl) Acrylic acid 2- hydroxy propyl esters, (methyl) acrylic acid 4- hydroxybutyls, the own ester of (methyl) acrylic acid 6- hydroxyls, (methyl) acrylic acid 8- Hydroxyl monooctyl ester etc., or hydroxy alkylidene glycol (methyl) acrylate, such as 2- hydroxyls ethylene glycol (methyl) acrylate, 2- Hydroxyl propane diols (methyl) acrylate etc.；Nitrogen containing monomer, such as (methyl) acrylonitrile, (methyl) acrylamide, N- methyl (first Base) acrylamide, N- butoxymethyls (methyl) acrylamide, NVP, N- caprolactams etc.；Bag Monomer containing epoxyalkane, such as alkoxyalkylene glycol (methyl) acrylate, the aklylene glycol of alkoxy two (methyl) Acrylate, the aklylene glycol of alkoxy three (methyl) acrylate, the aklylene glycol of alkoxy four (methyl) acrylate, alkane Epoxide polyethylene glycol (methyl) acrylate, phenoxy group aklylene glycol (methyl) acrylate, the aklylene glycol of phenoxy group two (methyl) acrylate, the aklylene glycol of phenoxy group three (methyl) acrylate, the aklylene glycol of phenoxy group four (methyl) propylene Acid esters, phenoxy group PAG (methyl) acrylate etc.；The monomer of styrene-based, such as styrene or methylbenzene second Alkene；Monomer comprising glycidyl, such as (methyl) glycidyl acrylate；Vinyl esters of carboxylic acids, such as vinyl acetate Base ester etc..
Typical polymerization can be used to prepare for this acrylic psa resin, for example, by will be via The monomer mixture for mixing suitable monomer according to desired monomer composition and preparing is applied to solution polymerization process.In this method In, if necessary, suitable polymerization initiator, molecular weight regulator, chain-transferring agent etc. can be used together.
Cross-linkable composition can additionally comprise crosslinking agent, the crosslinking agent for specifically enabling pressure sensitive adhesive resin be crosslinked. The example of crosslinking agent includes having two or more can be anti-with the carboxyl included in acrylic psa resin The compound for the functional group answered.As such crosslinking agent, crosslinking agent commonly used in the art, such as the friendship based on epoxy can be used Join agent or the crosslinking agent based on aziridine.Specifically, can enumerate selected from following one or more：Ethylene glycol diglycidyl Ether, triglycidyl ether, trihydroxymethylpropanyltri diglycidyl ether, N, N, N ', N '-four glycidyl group ethylenediamine, glycerine two Glycidol ether, N, N '-Toluene-2,4-diisocyanate, 4- double (1- aziridine formamide), N, N '-diphenyl methane -4,4 '-bis- (1- aziridine Formamide), triethylene melamine, double isophthalic diformyl -1- (2- methylaziridines) (bisisoprothaloyl- 1- (2-methylaziridine)) and three -1- '-aziridino phosphine oxides, but the application not limited to this.Based on 100 parts by weight Acrylic psa resin, such crosslinking agent can be included in the amount of 0.0001 parts by weight to 15 parts by weight and can handed over Join in composition, but not limited to this.In another embodiment, the ratio of crosslinking agent can be about 0.0005 parts by weight or bigger Or about 0.001 parts by weight or bigger.In another embodiment, the ratio of crosslinking agent can be 13 parts by weight or it is smaller, 11 Parts by weight or smaller, 9 parts by weight or smaller, 7 parts by weight or smaller, 5 parts by weight or smaller, 3 parts by weight or smaller, 1 parts by weight Or smaller, 0.5 parts by weight or smaller, 0.1 parts by weight or smaller, 0.05 parts by weight or smaller or 0.05 parts by weight or smaller.
If necessary, cross-linkable composition can additionally comprise ionic compound.Octanol-water partition coefficient (LogP), which may be selected, is 4 or bigger ionic compound as ionic compound.Octanol-water partition coefficient is represented in two kinds of unmixing pungent alcohol and waters The coefficient of solute distribution in phase.When by octanol-water partition coefficient be 4 or bigger ionic compound mixed with cross-linkable composition During conjunction, can be provided under high humidity or high temperature and high humidity has the stable antistatic property kept and surface is electric Hinder the cross-linkable composition not changed over time.In another embodiment, octanol-water partition coefficient can be 4.5 or bigger, 5 or bigger or 5.5 or bigger.Octanol-water partition coefficient is higher, to be ensured under high humility or high humility hot conditions from The stability of sub- compound is higher, therefore its upper limit is not particularly limited.In one embodiment, octanol-water partition coefficient Can be 30 or smaller, 25 or smaller, 20 or smaller or 15 or smaller.
Ionic compound can also include the cation that cation-water combination can be 0Kcal/mol to 0.6Kcal/mol.This In the range of combination can be for ensuring that stability of the ionic compound under high humidity or high temperature and high humidity is that have Profit.In another embodiment, cation-water combine can about 0Kcal/mol to 0.55Kcal/mol, 0.1Kcal/mol is to 0.55Kcal/mol, 0.2Kcal/mol to 0.55Kcal/mol or 0.3Kcal/mol to 0.55Kcal/ In the range of mol.
As ionic compound, any of compound can be used, as long as the octanol-water partition coefficient of the compound exists In above range, and cation-water is combined and can limited within the above range without special if necessary.
In one embodiment, comprising can be used as ionic compound with the ionic compound of the cation of following formula 7.
[formula 7]
In formula 7, R1Represent the alkyl with 1 to 3 carbon atom, and R2To R4Represent there is 4 to 20 independently of one another The alkyl of individual carbon atom.
In formula 7, R1To R4Linear, branched or cyclic alkyl, and preferably linear alkyl can be represented.In addition, alkyl can Arbitrarily substituted by another substituent such as alkyl.
In another embodiment, in formula 7, R2To R4It each can independently represent there is 4 to 16,4 to 12 or 4 to 8 The alkyl of individual carbon atom.
Cation as described above has wherein nitrogen-atoms and 4 alkyl linked structures, and wherein 3 alkyl are tool There is the chain alkyl of 4 or more carbon atoms, and the cation having a structure in which is for ensuring octanol-water disposition Number and cation-water, which combine, to be favourable within the above range.
The example of the cation of formula 7 includes N- methyl-N, N, N- tributyl ammonium, N- ethyls-N, N, N- tributyl ammonium, N- first The hexyl ammonium of base-N, N, N- tri-, the hexyl ammonium of N- ethyls-N, N, N- tri-, N- methyl-N, N, N- trioctylammonium, N- ethyls-N, N, N- tri- Octyl group ammonium etc., but not limited to this.
The example of anion included in ionic compound includes PF6 -, hexafluoro arsinic acid root (AsF-), nitrite anions (NO2 -), fluorine ion (F-), chlorion (Cl-), bromide ion (Br-), iodide ion (I-), perchlorate (ClO4 -), hydroxyl (OH-), carbonate (CO3 2-), nitrate anion (NO3 -), trifluoromethanesulfonic acid root (CF3SO3 -), sulfate radical (SO4 -), hexafluoro-phosphate radical (PF6 -), toluene sulfonic acide root (CH3(C6H4)SO3 -), p-methyl benzenesulfonic acid root (CH3C6H4SO3 -), tetraboric acid root (B4O7 2-), carboxyl Benzene sulfonic acid root (COOH (C6H4)SO3 -), trifluoromethanesulfonic acid root (CF3SO2 -), benzoate anion (C6H5COO-), acetate (CH3COO-), trifluoroacetic acid root (CF3COO-), tetrafluoroborate (BF4 -), tetrabenzyl borate (B (C6H5)4 -), three (five fluorine second Base) trifluoro phosphate radical (P (C2F5)3F3 -) etc., without especially limitation.
In one embodiment, ionic compound can include the anion or double (fluorosulfonyl) by being represented with following formula 8 Acid imide.
[formula 8]
[X(YOmRf)n]-
In formula 8, X represents nitrogen-atoms or carbon atom, and Y represents carbon atom or sulphur atom, RfRepresent perfluoroalkyl, m be 1 or 2 and n is 2 or 3.
In formula 8, when Y is carbon, m can be 1, and when Y is sulphur, m can be 2, and when X is nitrogen, n can be 2, and when X is During carbon, n can be 3.
The anion of formula 8 or double (fluorosulfonyl) acid imides are due to perfluoroalkyl (Rf) or fluorin radical and show high electricity Negativity, and the resonant structure of uniqueness is included, it forms weak bond with cation, so as to have hydrophobicity.Therefore, ionic compound It can show the compatibility excellent with another component such as polymer of composition, and can be high anti-quiet to provide on a small quantity Electric energy power.
The R of formula 8fIt can be the perfluoroalkyl with 1 to 20,1 to 12,1 to 8 or 1 to 4 carbon atom.In this case, Perfluoroalkyl can have linear, branched or cyclic structure.The anion of formula 8 may be based on sulfonyl methide, based on sulphonyl Base acid imide, based on carbonvlmethyl compound or based on the imido anion of carbonyl, and specifically, three trifyl first Glycolylate, double trifyl acid imides, double perfluorobutanesulfonyl acid imides, double five fluorine ethylsulfonyl acid imides, three trifluoros It is one or two kinds of or more in first carbonvlmethyl compound, fluorine fourth carbonyl acid imide of enjoying a double blessing, double five fluorine B carbonyl acid imides etc. The mixture of kind.
The ratio of ionic compound in cross-linkable composition is not particularly limited, and is contemplated that desired antistatic Characteristic etc. and adjust to suitable scope.
In cross-linkable composition as described above, ionic compound and polyalkylene polyol compound can substantially not Form chelate.In addition, in cross-linkable composition, polyalkylene polyol compound is to acrylic psa resin Can have than the compatibility higher to ionic compound.
Polyalkylene polyol compound included in cross-linkable composition may be selected to be with it is explained below with The combination energy or hybrid energy of acrylic psa resin, crosslinking agent and ionic compound.
Although being not particularly limited, it was found by the inventors of the present invention that by controlling polyalkylene polyol compound (its For the compound with polyalkylene oxide units) hydroxyl value and molecular weight, can more easily meet energy explained below Relation.
Term " polyalkylene oxide or PAG " as used in this article, which can refer to have comprising two or more, to be contained There is the object of linear or sub-branched alkyl the oxide units of 2 to 12 carbon atoms.In the above description, alkylidene can have There are 2 to 8,2 to 4 or 2 or 3 carbon atoms.
In this application, the instantiation of polyalkylene oxide includes PEO or PPOX, PAG Instantiation include polyethylene glycol or polypropylene glycol.
In this application, the compound for having polyalkylene oxide unit and/or PPOX unit can be used as poly- alkylene Polylol compound.
Polyalkylene polyol compound can be for example with such as 3 or more end hydroxyls of 3 or more hydroxyls The compound of base.Hydroxyl value included in polyalkylene polyol compound can be 30 or less for example, terminal hydroxyl number, 25 or less, 20 or less, 15 or less, 10 or less or 5 or less.
In addition, the polymer compound that molecular weight is 10000 or higher can be used as polyalkylene polyol compound.At this In application, term " weight average molecular weight " refer to by gel permeation chromatography (GPC) measure relative to polystyrene standard Conversion values.Unless otherwise specified, otherwise term " molecular weight " used herein refers to weight average molecular weight.In another reality Apply in scheme, molecular weight can be 100000 or smaller, 90000 or smaller, 80000 or smaller, 70000 or smaller, 60000 or more It is small, 50000 or smaller or 40000 or smaller.
In this application, it can more suitably meet that energy closes by selecting above-mentioned polyalkylene polyol compound System.
Suitable polyalkylene polyol compound can be but be not limited to the compound by being represented with following formula 1 in the application.
[formula 1]
In formula 1, A is the core comprising polyalkylene oxide units, and B is to be connected and comprising polyalkylene oxide units with the core (A) Chain, m is 1 or bigger integer, and n is 0 or bigger integer, and m and n summation (m+n) is 3 or bigger.
In one embodiment, the core (A) in formula 1 can be the core of derivative polyalkylene polyols.For example, formula 1 Compound can pass through the chain (B) in one or more hydroxyl adding types 1 by means of polyalkylene polyol compound end And formed.The polyalkylene polyol compound for forming core (A) can be triol or higher level polyalcohol, i.e., comprising 3 or more The compound of individual terminal hydroxyl, and chain (B) can be added by means of at least one hydroxyl therein.Form the poly- Asia of core (A) Alkyl polyols compound can include 3 or more terminal hydroxyls.Hydroxyl included in polyalkylene polyol compound Number can be 30 or less, 25 or less, 20 or less, 15 or less, 10 or less or 5 or less.Therefore, in formula 1 N and m summation (n+m) can be 3 or bigger, and be alternatively 30 or smaller, 25 or smaller, 20 or smaller, 15 or smaller, 10 It is or smaller or 5 or smaller.
On the other hand, the compound of formula 1 is alternatively as the change for including polyalkylene oxide units and 3 or more hydroxyl The polyalkylene polyol compound of compound.
It is explained below on the molecular weight of the core (A) in formula 1 and PEO and PPOX etc. in formula 1 In core (A) in the details comprising form can be the polyalkylene polyol compound to form core (A) molecular weight, Yi Jiju Oxirane and PPOX include form in the polyalkylene polyol compound for forming core (A).
In the compound of formula 1, the weight average molecular weight of core (A) can be 1000 to 40000.In another embodiment, The molecular weight of core (A) can be 2000 or bigger, 3000 or bigger, 4000 or bigger, 5000 or bigger or 6000 or bigger.Separately Outside, in another embodiment, the molecular weight of core (A) can be 35000 or smaller, 30000 or smaller, 25000 or smaller, 20000 or smaller, 15000 or smaller, 10000 or smaller or about 9000 or smaller.
In the compound of formula 1, core (A) can include polyalkylene oxide unit or PPOX unit, and at one In embodiment, core (A) can include both described units.When core (A) includes both described units, in the compound of formula 1, The ratio (P/E) of the molal quantity (P) of PPOX unit in core and the molal quantity (E) of polyalkylene oxide unit can be 1 to 10.In another embodiment, can be 1.5 or bigger, two or more, 2.5 or bigger, 3 or bigger, 3.5 or more than (P/E) It is big or 4 or bigger.In another embodiment, can be 9.5 or smaller, 9 or smaller, 8.5 or smaller, 8 or more than (P/E) It is small, 7.5 or smaller, 7 or smaller, 6.5 or smaller, 6 or smaller, 5.5 or smaller or about 5 or smaller.
As the above-mentioned polyalkylene polyol compound that can form core, it is referred to as KPX PP- for example, can enumerate 2000th, KPX PP-2600, KPX GP-4000, KPX-GP-5000, KPX GP-4000 or KPX-HP3753 etc. polyalkylene Polyol compound, but the application not limited to this.
In formula 1, core (A) and chain (B) can each include one or more polyalkylene oxide units.
In the above description, the concrete form of polyalkylene oxide units is as described above.
This polyalkylene oxide units can be for example by being represented with following formula 3.
[formula 3]
In formula 3, as described above, L can be the linear or sub-branched alkyl with 2 to 12,2 to 8 or 2 to 4 carbon atoms, Or the linear or sub-branched alkyl with 2 or 3 carbon atoms.
In the compound of formula 1, the chain (B) added to core (A) can be for example by being represented with following formula 2.
[formula 2]
In formula 2, A1To A3Alkylidene, Q are represented independently of one another1And Q2Represent aliphatic series or aromatics residue of divalent, L1To L4 Linking group is represented, x is 1 or bigger integer, and y is 0 or bigger integer, and z is 1 or bigger integer.
In formula 2, L1It can be bonded with core (A).
In formula 2, alkylidene can be the linear or sub-branched alkyl for example with 2 to 12,2 to 8 or 2 to 4 carbon atoms. For example, alkylidene can be ethylidene or propylidene.Alkylidene arbitrarily can be substituted by one or more substituents.
In formula 2, A1Or A2The polycyclic of formula 3 can be formed with connected oxygen atom (repeat unit limited by x or z) Oxygen alkane unit.
In formula 2, L1To L4The type of linking group be not particularly limited, and for example, can be oxygen atom, sulphur atom, Alkylidene, alkenylene or alkynylene, or can be the linking group by being represented with following formula 4 or 5.In the above description, alkylidene Can be the linear or sub-branched alkyl with 1 to 20,1 to 16,1 to 12,1 to 8 or 1 to 4 carbon atom, and alkenylene or Asia Alkynyl can be linear or branched alkenylene group or alkynylene with 2 to 20,2 to 16,2 to 12,2 to 8 or 2 to 4 carbon atoms.
[formula 4]
[formula 5]
In formula 4 and 5, R1And R2Hydrogen atom or alkyl are represented independently of one another.
In formula 4 and 5, alkyl can be the line for example with 1 to 20,1 to 16,1 to 12,1 to 8 or 1 to 4 carbon atom Property, branched or cyclic alkyl, and the alkyl arbitrarily can be substituted by one or more substituents.
In formula 2, alicyclic or aromatics residue of divalent can be the divalence derived from alicyclic compound or aromatic compounds Residue.
In the above description, aromatic compounds can refer to one of benzene or two or more phenyl ring by sharing it One or two carbon atom and the compound of structure to bond together, there is two of which or more phenyl ring to pass through any connection The compound for the structure that group bonds together, or derivatives thereof.Aromatic compounds can be for example with 6 to 30,6 to 25,6 to 21st, 6 to 18 or 6 to 13 carbon atoms compound.
In the above description, alicyclic compound refers to the compound with cyclic hydrocarbon structures, rather than has aromatic ring The compound of structure.Unless otherwise specified, otherwise alicyclic compound can be for example with 3 to 30,3 to 25,3 to 21,3 To 18 or the compound of 3 to 13 carbon atoms.
In formula 2 ,-L1-Q1-L2- or-L3-Q2-L4- structure can be the structure derived from diisocyanate cpd.
In the above description, the example of diisocyanate cpd includes toluene di-isocyanate(TDI), the isocyanic acid of dimethylbenzene two Ester, methyl diphenylene diisocyanate, hexamethylene diisocyanate, IPDI, tetramethyl xylene two Isocyanates, naphthalene diisocyanate etc., but not limited to this.
In one embodiment, the chain (B) of the compound of formula 1 can be by being represented with following formula 6.
[formula 6]
In formula 6, A1To A3Alkylidene, Q are represented independently of one another1And Q2Represent aliphatic series or aromatics residue of divalent, R1To R4 Hydrogen atom or alkyl are represented independently of one another, and x is 1 or bigger integer, and y is 0 or bigger integer, and z is 1 or bigger Integer.
The structure of formula 6 is the linking group L wherein in formula 21To L4The structure specified by formula 4 or 5.
Can be identical with formula 2 accordingly, with respect to the details of the alkylidene in formula 6, residue of divalent or linking group.
In addition, in formula 2 and 6, x, y and z specific scope are not particularly limited, and for example, x, y and z can be wherein The compound of formula 1 selects in the range of can having molecular weight explained below.
The compound of formula 1 can be for example by making between polyalkylene glycol compounds and diisocyanate cpd It is anti-to react above-mentioned polyalkylene polyol compound of the chain with formation core (A) and comprising 3 or more terminal hydroxyls obtained It should prepare.
For example, as the reaction for preparing chain, when polyethylene glycol and IPDI reaction, can be had The wherein one end such as represented using following formula A is the precursor of hydroxyl and the other end as the chain of the structure of isocyanate groups.
[formula A]
For example, the precursor when formula A chain and the three alcoholic compounds reaction with following formula B so that all hydroxyls of formula B triol When being reacted with the isocyanate groups of the end of formula A chain to add chain, it can be formed with such as with the change of the following formula C structures represented Compound.In this case, can be the core (A) in formula 1 with the P in following formula B and C.
[formula B]
[formula C]
This compound of formula 1 can include 3 moles or more of hydroxyl.In another embodiment, included in formula 1 The molal quantity of hydroxyl in compound can be 30 or smaller, 25 or smaller, 20 or smaller, 15 or smaller, 10 or smaller or 5 or It is smaller.
In another embodiment, the hydroxyl value of the compound of formula 1 can be 4mgKOH/g or bigger.In another embodiment party In case, hydroxyl value can be 30mgKOH/g or smaller, 25mgKOH/g or smaller, 20mgKOH/g or smaller or 15mgKOH/g or more It is small.
In the above description, hydroxyl value can be according to ASTM E222-10 (using the standard method of test of the hydroxyl of acetic anhydride) meter Calculate.
The compound of formula 1 can be that molecular weight is 10000 or bigger polymer compound.In another embodiment, Molecular weight can be 100000 or smaller, 90000 or smaller, 80000 or smaller, 70000 or smaller, 60000 or smaller, 50000 It is or smaller or 40000 or smaller.
The ratio of polyalkylene polyol compound in cross-linkable composition is not particularly limited, and is contemplated that and expires Interfacial adhesion improvement of prestige etc. and suitably adjust.For example, the acrylic psa tree based on 100 parts by weight Fat, the polyalkylene polyol compound of 0.01 parts by weight or more can be included.In another embodiment, polyalkylene is more The ratio of first alcoholic compound can be about 0.02 parts by weight or bigger, about 0.03 parts by weight or bigger, about 0.04 parts by weight or it is bigger, Or about 0.04 parts by weight or bigger.In addition, in another embodiment, the ratio of polyalkylene polyol compound can be About 10 parts by weight or smaller, about 9 parts by weight or smaller, about 8 parts by weight or smaller, about 7 parts by weight or smaller, about 6 parts by weight or Smaller, about 5 parts by weight or smaller, about 4 parts by weight or smaller, about 3 parts by weight or smaller, about 2 parts by weight or smaller, about 1 weight Part or smaller, about 0.5 parts by weight or smaller, about 0.4 parts by weight or smaller, about 0.3 parts by weight or smaller, about 0.2 parts by weight or Smaller or about 0.1 parts by weight or smaller.
Each component in the application may be selected so that its energy relationship is as follows.
For example, in this application, the knot between polyalkylene polyol compound and acrylic psa resin Energy (A) is closed to be controllable to less than the combination energy (B) between the crosslinking agent and acrylic psa resin in composition.It is logical Such control is crossed, polyalkylene polyol compound can be higher than acrylic acid to the compatibility of acrylic psa resin Class pressure sensitive adhesive resin is to the compatibility of crosslinking agent, it is possible thereby to adjust crosslinking speed by polyalkylene polyol compound Degree.
In one embodiment, the combination between crosslinking agent and acrylic psa resin can (B) and poly- Asia The difference (B-A) of combination energy (A) between alkyl polyols compound and acrylic psa resin can be 2Kcal/mol Or bigger, 2.2Kcal/mol or bigger or 2.3Kcal/mol or bigger.In addition, in another embodiment, with reference to energy Difference (B-A) can be 20Kcal/mol or smaller, 18Kcal/mol or smaller, 16Kcal/mol or smaller, 14Kcal/mol or Smaller, 12Kcal/mol or smaller, 10Kcal/mol or smaller, 8Kcal/mol or smaller, 6Kcal/mol or smaller, 4Kcal/ Mol or smaller or 3.5Kcal/mol or smaller.Polyalkylene polyol compound can be poor by combining energy as described above Suitably adjust the speed of cross-linking reaction.
In the above description, the combination energy (B) between crosslinking agent and acrylic psa resin can be -7Kcal/ Mol or bigger.In another embodiment, it can be about -1Kcal/mol or smaller, -2Kcal/mol or more with reference to energy (B) Small, -3Kcal/mol or smaller, -4Kcal/mol or smaller or -5Kcal/mol or smaller.
In addition, the combination energy (A) between acrylic psa resin and polyalkylene polyol compound can be small In -7Kcal/mol.In another embodiment, it can be about -7.5Kcal/mol or smaller or -8Kcal/ with reference to energy (A) Mol or smaller.In addition, in another embodiment, it can be about -20Kcal/mol or bigger, -18Kcal/ with reference to energy (A) Mol or bigger, -16Kcal/mol or bigger, -14Kcal/mol or bigger, -12Kcal/mol or bigger, -10Kcal/mol or More greatly or about -9Kcal/mol or bigger.
Make combine can within the above range, polyalkylene polyol compound can suitably adjust the speed of cross-linking reaction Degree.
In addition, in cross-linkable composition, ionic compound and polyalkylene polyol compound can not formed substantially Chelate.That is, when ionic compound has high-affinity to polyalkylene polyol compound, suppress or adjust acrylic compounds Polyalkylene polyol compound needed for cross-linking reaction between pressure sensitive adhesive resin and crosslinking agent is due to the ionization Compound and its function can not be appropriately performed.
Therefore, may be selected ionic compound cause hybrid energy between ionic compound and ethylene oxide unit for- 2Kcal/mol or bigger.In another embodiment, hybrid energy can be -1.8Kcal/mol or bigger, -1.6Kcal/mol Or bigger, -1.4Kcal/mol or more greatly or about -1.2Kcal/mol or bigger.In addition, hybrid energy can be about -0.1Kcal/ Mol or smaller, about -0.2Kcal/mol or smaller, -0.3Kcal/mol or smaller, -0.4Kcal/mol or smaller, - 0.5Kcal/mol or smaller, -0.6Kcal/mol or smaller, -0.7Kcal/mol or smaller or about -0.8Kcal/mol or more It is small.
Hybrid energy is the hybrid energy calculated between ionic compound and a mol ethylenoxy.As described above, make Polyalkylene oxide units are included for the polyalkylene polyol compound of crosslinking rate conditioning agent.Therefore, ionic compound and epoxy Hybrid energy between ethylene oxide units can represent ionic compound and polyalkylene polyol compound (crosslinking rate conditioning agent) it Between compatibility.By controlling the hybrid energy between ionic compound and ethylene oxide unit as described above, ion can be prevented Compound interference adjusts crosslinking rate by polyalkylene polyol compound.
The method of energy state between the component that control is included in as above cross-linkable composition is not particularly limited.For example, Component can be selected from the main constituent of cross-linkable composition and enables its combination with above-mentioned combination or hybrid energy.
In addition to the foregoing, other components can also be included according to purposes, cross-linkable composition.
For example, cross-linkable composition can additionally comprise isocyanate compound.Cross-linkable composition is applied to for example, working as During optical element explained below, the compound can be used for improving the cohesive with optical element.Change based on isocyanates The instantiation of compound includes being selected from following one or more：Toluene di-isocyanate(TDI), XDI, hexichol Dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, IPDI, the isocyanic acid of tetramethyl xylene two Ester, naphthalene diisocyanate and its reaction product with polyhydric alcohols such as trimethylolpropane, but not limited to this.Based on 100 weight The acrylic psa resin of part, isocyanic acid can be based on comprising such with the amount of 0.01 parts by weight to 10 parts by weight The compound of ester, but not limited to this.In another embodiment, the ratio of isocyanate compound can be about 0.05 parts by weight Or bigger, about 0.01 parts by weight or bigger, 0.1 parts by weight or bigger, 0.5 parts by weight or bigger or about 1 parts by weight or bigger. In another embodiment, the ratio of crosslinking agent can be 8 parts by weight or smaller, 6 parts by weight or smaller, 4 parts by weight or smaller Or 3.5 parts by weight or smaller.
In addition to the foregoing, cross-linkable composition, which can also include, is selected from following one or more of additions Agent：Silane coupler, tackifier, epoxy resin, crosslinking agent, UV light stabilizers, antioxidant, colouring agent, reinforcing agent, filler, Defoamer, surfactant and plasticizer.
In addition, the example as pressure-sensitive adhesion optical element, the application can relate to the polarisation coated through pressure sensitive adhesive layer Plate, it is comprised at least with the light polarizing film for forming the transparent protective film on one or two surface of polarization element；With it is pressure-sensitive Adhesive phase.
In the above description, the details on polarization element and transparent protective film is as described above.
In the above description, pressure sensitive adhesive layer is formed by above-mentioned cross-linkable composition, and for example, can be by being glued to be pressure-sensitive The cross-linkable composition of mixture composite is formed.
Cross-linkable composition can be comprising (methyl) acrylic polymer and have anionic group and cationic componentses Ionic compound pressure-sensitive adhesive composition.In the above description, (methyl) acrylic polymer can be aforesaid propylene Acrylic pressure sensitive adhesive resin, and ionic compound can also include above-mentioned cationic componentses and anionic group.
In one embodiment, (methyl) acrylic polymer of cross-linkable composition is aforesaid propylene acrylic pressure sensitive Adhesive resin, and can be containing aromatic ring with (methyl) alkyl acrylate containing aromatic ring as monomeric unit (methyl) acrylic polymer.There are 3 or more hydroxyls and divide equally again in addition, pressure-sensitive adhesive composition can also include Son amount is 10000 or bigger above-mentioned polyalkylene polyol compound.
When aforesaid propylene acrylic pressure sensitive adhesive resin includes (methyl) alkyl acrylate containing aromatic ring, it is based on The total monomer of 100 parts by weight, described contain can be included with the ratio of 5 parts by weight to 30 parts by weight or 10 parts by weight to 25 parts by weight (methyl) alkyl acrylate of aromatic ring.In addition to (methyl) alkyl acrylate containing aromatic ring, propylene can be formed The instantiation of the monomer of acrylic pressure sensitive adhesive resin is as described above.
In addition, the example of (methyl) alkyl acrylate containing aromatic ring include (methyl) acrylate or (methyl) benzyl acrylate, but not limited to this.
The application further relates to be attached with the display device of above-mentioned pressure-sensitive adhesion optical element.For example, described device may include Liquid crystal panel and be attached to the liquid crystal panel one or two surface optical element.
As liquid crystal panel, known panel, such as passive matrix panel such as twisted-nematic (TN), supertwist can be used Nematic (STN), ferroelectricity (F) or polymer disperse (PD) panel；Active array type panel such as two-terminal panel or three terminal panels, In-plane switching (IPS) panel or vertical orientated (VA) panel.Especially, when the above-mentioned contact adhesive of application, VA mode liquid crystals Panel can effectively serve as liquid crystal panel.
In addition, the miscellaneous part (for example, color filter substrate or upper substrate and lower substrate such as array substrate) of liquid crystal display Type be not particularly limited, and can be used any part known in the art without limit.
Effect
The application is related to pressure-sensitive adhesion Polarizer.In one embodiment, it is included in the pressure-sensitive adhesion polarisation of the application Pressure sensitive adhesive layer in plate shows excellent interfacial adhesion and no segregation phenomenon.
Brief description of the drawings
Fig. 1 and 2 shows infrared (IR) spectral results of the compound prepared in preparation example 2 and 3.
Embodiment
Hereinafter, the present invention will be described in detail with reference to embodiment and comparative example, it should be noted that contact adhesive group The scope of compound is not limited to following examples.
1. infrared (IR) spectrometry
The condition for the measurement IR spectrum applied in this manual is as follows.During measurement, spectrum baseline is air.
<Measuring condition>
Measuring instrument：Agilent Cary 660FTIR spectrometers
ATR：PIKE Technologies 025-2018Miracle ZnSe performance chips
Measure wavelength：400nm to 4000nm
Measurement temperature：25℃
2. the evaluation of molecular weight
Measure weight average molecular weight (Mn) under the following conditions using GPC.When preparing calibration curve, Agilent is used System polystyrene standard converted measurement result.
<Measuring condition>
Measuring instrument：Agilent GPC (series of Agilent 1200, the U.S.)
Post：Two PL Mixed B of connection
Column temperature：40 DEG C of eluant, eluents：Tetrahydrofuran (THF)
Flow velocity：1.0mL/ minute
Concentration：About 1mg/mL (100 μ L of injection)
3. the measurement of acid number
Measurement acid number (COM-550, is manufactured) by HIRANUMA SANGYO Co., Ltd.s using automatic titration device, and is led to Cross below equation calculating：
A={ (Y-X) × f × 5.611 }/M
A；Acid number
Y；The titer (ml) of sample solution
X；The titer (ml) of solution comprising 50g mixed solvents
f；The factor of volumetric soiutions
M；The weight (g) of polymer samples
Measuring condition is as follows.
Sample solution：By by about 0.5g polymer samples be dissolved in 50g mixed solvents (toluene/2- propyl alcohol/distilled water= 50/49.5/0.5 weight ratio) in and prepare
Volumetric soiutions：0.1N, 2- propyl alcohol type potassium hydroxide solution (manufactured by Wako Junyaku Kogyo Co., Ltd.s, Neutralization number for oil product is tested)
Electrode：Glass electrode, GE-101, comparison electrode：RE-201
Measurement pattern：Neutralization number for oil product tests 1
4. the measurement of octanol-water partition coefficient
Octanol-water is calculated using the COSMOtherm (version C30_1301, COSMOlogic) for business thermodynamics program Distribution coefficient.The surface charge distribution and the difference in chemical potential of water and octanol of each compound are calculated using the program, is derived from Distribution coefficient (LogP).In this process, parameterized using BP_TZVP_C30_1301.
5. combine the measurement of energy
Use density functional theory (density functional theory, DFT) the calculating bag to be manufactured by BIOVIA DMoL3 (Materials Studio DMoL3 versions 6.1) calculations incorporated energy.Made using BP functions/DNP bases group (basis) For calculated level.To being modeled to combine two kinds of materials of the target of energy in individual molecule level, to obtain two of which The situation and the wherein optimum structure for the situation that they are combined, and calculate the energy of two kinds of situations that material each is present in gas phase Amount difference, which is used as, combines energy.
6. the measurement of hybrid energy
Using the COSMOtherm (version C30_1301) for COSMO-RS theoretical calculation bags and for by COSMOlogic The Turbomole (version 6.5) that the DFT of GmbH＆Co.KG manufactures calculates bag calculates hybrid energy.In COSMOtherm, use BP_TZVP_C30_1301 is parameterized, and BP functions/def-TZVP base groups are used in Turbomole.In individual molecule water Every kind of material of the target for hybrid energy is modeled on flat, and the use of Turbomole bags is nothing in surrounding dielectric constant Optimum structure and surface shielded packaged food are calculated in poor big environment, and is based on this, calculates wherein each self-existent feelings of material Chemical potential under condition and wherein they mix in the case of chemical potential difference as hybrid energy.In the case of logP, entering After row identical process, also hybrid energy is calculated using COSMOtherm.
7. the measurement of durability
The Polarizer of embodiment or comparative example is cut into about 262mm × about 465mm (width x length) size to prepare two Piece sample, and the two panels sample thus prepared is attached to two surfaces of substrate of glass, wherein the light absorbs axle of each Polarizer Intersect, so as to prepare sample.The pressure applied during attachment is about 5kg/cm2, and this is operated in toilet and carried out so that not Introduce bubble or foreign matter.
Pass through the durability of resistance to heat durability and wet-heat resisting durability evaluation sample.By sample 60 DEG C temperature and Evaluation moisture-proof heat durability, is placed by sample at a temperature of 80 DEG C after being placed under 90% relative humidity about 500 hours Resistance to heat durability is evaluated after about 500 hours.
The evaluation criterion of durability is as follows.
<Evaluation criterion>
O：Bubble and stripping are not observed when evaluating heat-resisting and moisture-proof heat durability
Δ：A small amount of bubble and/or stripping are observed when evaluating heat-resisting and/or moisture-proof heat durability
X：Numerous air-bubble and/or stripping are observed when evaluating heat-resisting and/or moisture-proof heat durability
8. the measurement of the sheet resistance of pressure sensitive adhesive layer
The Polarizer prepared in embodiment or comparative example is placed 7 days and measured under 25 DEG C and 50%RH of room temperature condition Sheet resistance (initial surface resistivity).Mould release membrance is being removed from Polarizer and is using HIRESTA-UP (MCP-HT450；By Mitsubishi Chemical Corporation are manufactured) apply 500V voltage 1 minute in the environment of 23 DEG C and 50%RH Measurement surface resistance afterwards.Sample (pressure-sensitive adhesion Polarizer) is placed at 80 DEG C to 1000 hours to measure sample in heat-resisting bar Sheet resistance under part, and sample (pressure-sensitive adhesion Polarizer) is placed 1000 hours to measure sample under 60 DEG C and 90%RH Sheet resistance under the conditions of wet-heat resisting.After each sample is placed into 24 hours at room temperature, to be placed on as above it is heat-resisting and Sample under the conditions of wet-heat resisting is evaluated.
9. the evaluation of mist degree
Pass through the painting that detected by an unaided eye immediately after the pressure-sensitive adhesive composition prepared in coating embodiment or comparative example The state of solution is covered to evaluate mist degree.Evaluated according to following standard.
<Evaluation criterion>
O：It is not it was observed that muddy
Δ：It was observed that little cloudy
X：It is it was observed that serious muddy
10. evaluate the evaluation of peel strength
The pressure-sensitive adhesion Polarizer prepared in embodiment or comparative example is cut into the chi of 25mm × 120mm (width x length) It is very little, and it is attached to substrate of glass by means of pressure sensitive adhesive layer.After attachment 4 hours, with the peel angle of 180 degree and 300mm/ points The peeling rate of clock gradually peels off Polarizer to measure peel strength (initial bonding strength) from substrate of glass.In addition, After attachment, Polarizer is placed 4 hours at 50 DEG C, and measures peel strength (50 DEG C of peel strengths) in an identical manner.
11. the evaluation of substrate adhesiveness
The substrate adhesiveness for evaluating pressure-sensitive adhesion Polarizer by the following method (is protected between pressure sensitive adhesive layer and Polarizer Cohesive between cuticula (TAC film)).Strong adhesive tape is attached to first to be formed on a surface of pressure-sensitive adhesion Polarizer On pressure sensitive adhesive layer surface on.Strong adhesive tape is peeled off from pressure-sensitive adhesion Polarizer in 1 minute after laminated, surveyed The amount for the pressure sensitive adhesive layer that amount is retained in polarisation plate surface after peeling off simultaneously is based on following criteria classification.
<Evaluation criterion>
O：The Polarizer gross area 90% or remain with pressure sensitive adhesive layer more greatly
Δ：The Polarizer gross area 50% or bigger and remain with pressure sensitive adhesive layer less than 90%
X：The Polarizer gross area remains with pressure sensitive adhesive layer less than 50%
12. release peel strength at room temperature
The pressure-sensitive adhesion Polarizer prepared in embodiment or comparative example is cut into the chi of 50mm × 120mm (width x length) It is very little.Thereafter, using two-sided tape by the surface attachment without pressure sensitive adhesive layer of the pressure-sensitive adhesion Polarizer of cutting to glass In glass substrate.Then, with the peeling rate of the peel angle of 180 degree and 300mm/ minutes by the mould release membrance on pressure sensitive adhesive layer Peel off to measure peel strength (initial bonding strength).
The preparation of the acrylic psa resin solution of preparation example 1.
Through nitrogen reflux and it is being provided with 1L reactors of the cooling device easily to adjust temperature, with 94:6 weight ratio (BA:AA n-butyl acrylate (BA) and acrylic acid (AA)) are introduced, and also introduces ethyl acetate thereto as solvent.With Afterwards, 1 hour is purged except deoxidation by using nitrogen, introduce reaction initiator (AIBN：Azodiisobutyronitrile) and react about 8 hours. Then, with ethyl acetate diluting reaction thing using prepare acid number as about 32 to 34 and weight average molecular weight (Mw) be about 1800000 third Olefin(e) acid class pressure sensitive adhesive resin solution.
The preparation of the compound (A) of the formula 1 of preparation example 2.
In through nitrogen reflux and installation having heaters, cooling device and thermometer easily to adjust the reactor of temperature, With about 5:2.8 weight ratio (PEG:IPDI the polyethylene glycol (PEG) and isophorone two that) introducing weight average molecular weight is about 400 are different Cyanate, and temperature is slowly raised to about 50 DEG C and kept.In such a state, mixture is uniformly mixed and reacted about 1 hour.Reaction time is determined by IR spectrum, and continues reaction up to the 2270cm in IR spectrum before the reaction-1Place is found The area at NCO peaks be decreased to 50%.
Then, make reactant with polyol reaction with the compound (A) of formula 1.In the above description, using dividing equally again The polyol compound (HP-3753, being manufactured by KPX CHEMICAL CO., LTD.) that son amount is about 7000 is used as polyalcohol, its For three terminal hydroxyls of having of the PPOX unit comprising 85 weight % and 15 weight % polyalkylene oxide unit Three alcoholic compounds.
By polyol compound, reactant and catalyst (dibutyl tin laurate) with 92.1:7.8:0.003 weight Than (polyol compound:Reactant:Catalyst) mixing, and mixture is gradually added drop-wise to the reaction that temperature is maintained at about 60 DEG C Gone forward side by side in device single step reaction, so as to the compound (A) of formula 1.Continue reaction until NCO peaks are wholly absent in IR spectrum.
Thus the molecular weight (Mw) of the compound (A) prepared is about 15200 and hydroxyl value (OHv) is about 11.2mgKOH/g.System The IR spectrum of standby compound are as shown in Figure 1.
Preparation example 3：The preparation of the compound (B) of formula 1
In through nitrogen reflux and installation having heaters, cooling device and thermometer easily to adjust the reactor of temperature, With about 13.6:7.6 weight ratio (PEG:IPDI the polyethylene glycol (PEG) and isophorone that weight average molecular weight is about 400) are introduced Diisocyanate, and temperature is slowly raised to about 50 DEG C and kept.In such a state, mixture is uniformly mixed and anti- Should be about 1 hour.Reaction time is determined by IR spectrum, and continues reaction up to the 2270cm in IR spectrum before the reaction-1Place It was found that the area at NCO peaks be decreased to 50%.
Then, make reactant with polyol reaction with the compound (A) of formula 1.In the above description, using dividing equally again The polyol compound (HP-3753, being manufactured by KPX CHEMICAL CO., LTD.) that son amount is about 7000 is used as polyalcohol, its For three terminal hydroxyls of having of the PPOX unit comprising 85 weight % and 15 weight % polyalkylene oxide unit Three alcoholic compounds.
By polyol compound, reactant and catalyst (dibutyl tin laurate) with 78.9:21.2:0.009 weight Amount is than (polyol compound:Reactant:Catalyst) mixing, and mixture is gradually added drop-wise to temperature and is maintained at about 60 DEG C anti- Single step reaction of being gone forward side by side in device is answered, so as to the compound (B) of formula 1.Continue reaction until NCO peaks disappear completely in IR spectrum Lose.
Thus the molecular weight (Mw) of the compound (B) prepared is about 28900 and hydroxyl value (OHv) is about 5.61mgKOH/g.System The IR spectrum of standby compound are as shown in Figure 2.
Embodiment 1
Using with the methyltributylammoni,m and the conduct imido ion of anion trifyl as cation Compound is as ionic compound (octanol-water partition coefficient：About 5.65, cation-water combination energy：0.45Kcal/mol).Will Ionic compound, the acrylic psa resin of preparation example 1, crosslinking agent, the compound (A) of preparation example 2 and isocyanic acid Ester compounds are mixed to prepare cross-linkable composition.In the above description, using epoxy crosslinking agent (T-743L, by Nippon Soken Inc. are manufactured) crosslinking agent is used as, made using the addition polymerization by toluene di-isocyanate(TDI) and trimethylolpropane Standby compound (T-760B) is used as isocyanate compound.Acrylic psa resin based on 100 parts by weight is molten The solid content of liquid, by the crosslinking agent of 0.0052 parts by weight, the compound (A) of the preparation example 2 of about 0.0793 parts by weight, about 4 weight The ionic compound of part and the isocyanate compound mixing of about 2 parts by weight.Thus the cross-linkable composition prepared is applied to Release-treated poly- (ethylene glycol terephthalate) (PET, MRF-38, by Mitsubishi Chemical Corporation is manufactured) release-treated surface on and under suitable condition drying to form pressure sensitive adhesive layer.Will The pressure sensitive adhesive layer being consequently formed is laminated to the protection based on triacetyl cellulose (TAC) for being attached to two surface On one surface of the Polarizer based on iodine of film, so as to prepare pressure-sensitive adhesion Polarizer.The pressure-sensitive adhesion Polarizer has Wherein pressure-sensitive adhesion is sequentially formed on the TAC film on a surface of Polarizer (TAC film/polarization element/TAC film based on iodine) The structure of oxidant layer and mould release membrance.
Embodiment 2
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, Difference is the compound (A) that preparation example 2 is replaced using the compound (B) of preparation example 3.
Embodiment 3
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, Difference is to replace the compound (A) of preparation example 2 as poly- using the polyol compound that weight average molecular weight is about 7000 Aklylene glycol polyalcohol, it is the PPOX unit comprising 85 weight % and 15 weight % polyalkylene oxide unit Three alcoholic compounds with three terminal hydroxyls.
Comparative example 1
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, Difference is the compound (A) without using preparation example 2.
Comparative example 2
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, It is about 2000 using weight average molecular weight that difference, which is, and the polypropylene glycol with two terminal hydroxyls replaces the change of preparation example 2 Compound (A).
Comparative example 3
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, It is about 6000 using weight average molecular weight that difference, which is, and the polypropylene glycol with two terminal hydroxyls replaces the change of preparation example 2 Compound (A).
Comparative example 4
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, It is about 4000 using weight average molecular weight that difference, which is, and the polypropylene glycol with three terminal hydroxyls replaces the change of preparation example 2 Compound (A).
Comparative example 5
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, It is about 5000 using weight average molecular weight that difference, which is, and the polypropylene glycol with three terminal hydroxyls replaces the change of preparation example 2 Compound (A).
Comparative example 6
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, Difference is as known plasticizer, the use of weight average molecular weight is about 29000 and with the plasticising of a terminal hydroxyl Agent (L-7230) replaces the compound (A) of preparation example 2.
Comparative example 7
Cross-linkable composition, pressure sensitive adhesive layer and pressure-sensitive adhesion Polarizer are prepared in the same manner as in example 1, Difference be using the ratio of 0.00793 parts by weight using weight average molecular weight as about 29000 and with terminal hydroxyl Plasticizer (L-7230).
Embodiment and the result of comparative example are summarized in table 1 below and 2.
[table 1]
[table 2]

Claims (13)

1. a kind of pressure-sensitive adhesion Polarizer, including：
Polarization element；With
Pressure sensitive adhesive layer, it is formed on a surface of the polarization element and comprising with 3 or more hydroxyls And weight average molecular weight is 10000 or bigger polyalkylene polyol compound.
2. pressure-sensitive adhesion Polarizer according to claim 1, wherein the pressure sensitive adhesive layer is also included with carboxyl Acrylic psa resin and crosslinking agent.
3. pressure-sensitive adhesion Polarizer according to claim 1, wherein the polyalkylene polyol compound include by with The polyalkylene oxide units that following formula 3 represents：
[formula 3]
In formula 3, L is the linear or sub-branched alkyl with 2 to 12 carbon atoms.
4. pressure-sensitive adhesion Polarizer according to claim 1, wherein the polyalkylene polyol compound is by with following formula 1 Represent：
[formula 1]
In formula 1, A is the core comprising polyalkylene oxide units, and B is the chain by being represented with following formula 2, and m is 1 or bigger integer, n are 0 or bigger integer, and m and n summation (m+n) is 3 or bigger；
[formula 2]
In formula 2, A1To A3Alkylidene, Q are represented independently of one another1And Q2Represent aliphatic series or aromatics residue of divalent, L1To L4Represent Linking group, x are 1 or bigger integer, and y is 0 or bigger integer, and z is 1 or bigger integer.
5. the weight average molecular weight of the core of pressure-sensitive adhesion Polarizer according to claim 4, the wherein compound of formula 1 is 1000 to 10000.
6. the core (A) in pressure-sensitive adhesion Polarizer according to claim 4, wherein formula 1 includes PEO list Member and PPOX unit.
7. pressure-sensitive adhesion Polarizer according to claim 6, wherein the PPOX unit in the core rubs The ratio (P/E) of that number (P) and the molal quantity (E) of the polyalkylene oxide unit is 1 to 10.
8. the linking group in pressure-sensitive adhesion Polarizer according to claim 4, wherein formula 2 is oxygen atom, sulphur is former Son, alkylidene, alkenylene or alkynylene, or by being represented with following formula 4 or 5：
[formula 4]
[formula 5]
In formula 4 and 5, R1And R2Hydrogen atom or alkyl are represented independently of one another.
9. pressure-sensitive adhesion Polarizer according to claim 1, wherein the pressure sensitive adhesive layer also includes ionic compound.
10. pressure-sensitive adhesion Polarizer according to claim 9, wherein the octanol-water partition coefficient of the ionic compound For 4 or bigger.
11. pressure-sensitive adhesion Polarizer according to claim 9, wherein there is the ionic compound cation-water to combine It can be 0Kcal/mol to 0.6Kcal/mol cation.
12. pressure-sensitive adhesion Polarizer according to claim 1, wherein the pressure sensitive adhesive layer also includes isocyanation esterification Compound.
13. a kind of Polarizer coated through pressure sensitive adhesive layer, is comprised at least：
With the light polarizing film for forming the transparent protective film on one or two surface of polarization element；With
Pressure sensitive adhesive layer,
Wherein described pressure sensitive adhesive layer is by comprising (methyl) acrylic polymer and having anionic group and cation group The pressure-sensitive adhesive composition of the ionic compound divided is formed,
(methyl) acrylic polymer is as monomeric unit with (methyl) alkyl acrylate containing aromatic ring (methyl) acrylic polymer containing aromatic ring, and
The pressure-sensitive adhesive composition, which also includes, has 3 or more individual hydroxyls and weight average molecular weight is 10000 or bigger Polyalkylene polyol compound.
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